Ammonia → HCID 90308962, compound

HRID 2283704Notes

Reaction equation

HRID 2283704 reaction equation
C[N:2]1C(=O)CCC1.N.Br[C:10]1[CH:18]=[C:17]([CH3:19])[C:16]2[C:12](=[CH:13][N:14]([C:20]3([CH3:24])[CH2:23][CH2:22][CH2:21]3)[N:15]=2)[CH:11]=1>C(OCC)(=O)C.[Cu](I)I>[CH3:19][C:17]1[C:16]2[C:12](=[CH:13][N:14]([C:20]3([CH3:24])[CH2:23][CH2:22][CH2:21]3)[N:15]=2)[CH:11]=[C:10]([NH2:2])[CH:18]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 13387N-methyl-2-pyrrolidoneHCID 90308719HCID 90308719, compound

Product 1

HCID 90308962HCID 90308962, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Copper oxide (I) (50 mg), NMP (2.5 mL), and concentrated aqueous ammonia (2.5 mL) were added to 5-bromo-7-methyl-2-(1-methylcyclobutyl)-2H-indazole obtained in the above-described Step 1 (536 mg), and the reaction solution was stirred in a microwave reactor at 100° C. for 5 hours. The reaction solution was cooled to room temperature, diluted with ethyl acetate, and then washed successively with water three times and then with a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum, and the resultant was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain 7-methyl-2-(1-methylcyclobutyl)-2H-indazol-5-amine.

Workup

  1. customobtained in the above-described Step 1 (536 mg)
  2. temperatureThe reaction solution was cooled to room temperature
  3. washwashed successively with water three times
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. customthe solvent was evaporated under vacuum
  6. customthe resultant was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3e871b44b7f14e93bf0debd39a077958
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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